A Highly Chemoselective and Rapid Chlorination of Benzyl Alcohols under Neutral Conditions
Lili Sun, Guisheng Peng, Hongmei Niu, Qiang Wang, Chunbao Li*
*Department of Chemistry, College of Science, Tianjin University, Tianjin 300072, P. R. of China, Email: lichunbaotju.edu.cn
L. Sun, G. Peng, H. Niu, Q. Wang, C. Li, Synthesis, 2008, 3919-3924.
DOI: 10.1055/s-0028-1083243
Abstract
A rapid, selective, and high-yielding chlorination of benzylic alcohols in the presence of 2,4,6-trichloro-1,3,5-triazine and dimethyl sulfoxide takes 10 to 40 minutes. The neutral reaction conditions are compatible with substrates bearing acid-labile functional groups. Both competitive intramolecular and intermolecular reactions for benzyl alcohols in the presence of aliphatic alcohols indicate high selectivity.
see article for more examples
proposed mechanism
Key Words
benzyl alcohols, benzyl chlorides, chemoselectivity, halogenation, sulfoxides
ID: J66-Y2008-3720